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Chiral recognition applications of molecularly imprinted polymers: a critical review

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Abstract

Molecular imprinting technology offers the unique opportunity to tailor chiral stationary phases with predefined chiral recognition properties by employing the enantiomers of interest as binding-site-forming templates. Added advantages, such as ease of preparation, chemical robustness, low-cost production, and the possibility of shaping molecularly imprinted polymers (MIPs) in various self-supporting formats, render them attractive materials for a broad range of chiral recognition applications. In this review a critical overview on recent developments in the field of MIP-based chiral recognition applications is given, focusing on separation techniques and molecular sensing. Inherent limitations associated with the use of enantioselective MIP materials in high-performance separation techniques are outlined, including binding site heterogeneity and slow mass transfer characteristics. The prospects of MIP materials as versatile recognition elements for the design of enantioselective sensor systems are highlighted.

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Abbreviations

AcOH:

acetic acid

α1-AGP:

acidic glycoprotein

AIBN:

α,α-azoisobutyronitrile

Asp:

aspartic acid

Boc:

tert-butylcarboxycarbonyl protecting group

Bmax:

saturation loading capacity

CEC:

capillary electrochromatography

CSP:

chiral stationary phase

DCM:

dichloromethane

EDMA:

ethylene dimethacrylate

EOF:

electroosmotic flow

Fmoc:

9-Fluorenylmethoxycarbonyl protecting group

Glu:

glutamic acid

HPLC:

high-performance liquid chromatography

ITO:

indium tin oxide

ISFET:

ion-selective field-effect transistor

Kd:

dissociation constants

K POT :

potentiometric selectivity coefficient

MAA:

methacrylic acid

MeCN:

acetonitrile

MIP:

molecularly imprinted polymer

NIP:

non-imprinted control polymer

ODS:

octadecylsilane

OT:

open tubular

OVM:

ovomucoid

PA:

phenylalanine anilide

PBS:

phosphate-buffered saline

PETRA:

pentaerythritol triacrylate

Phe:

phenylalanine

QCM:

quartz-crystal microbalance

RAFT:

reversible addition–fragmentation chain transfer

RIfS:

reflectometric interference spectroscopy

SAW:

surface acoustic wave

SFC:

supercritical-fluid chromatography

SMB:

simulated moving bed

THF:

tetrahydrofuran

Trp:

tryptophan

TRIM:

2,2-bis(hydroxymethyl)butanol trimethacrylate

Tyr:

tyrosine

VPy:

4-phenylpyridine

Z:

benzyloxycarbonyl protecting group

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  1. Department of Analytical Chemistry and Food Chemistry, University of Vienna, Währinger Str. 38, 1090, Vienna, Austria

    Norbert M. Maier & Wolfgang Lindner

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  1. Norbert M. Maier
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  2. Wolfgang Lindner
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Maier, N.M., Lindner, W. Chiral recognition applications of molecularly imprinted polymers: a critical review. Anal Bioanal Chem 389, 377–397 (2007). https://doi.org/10.1007/s00216-007-1427-4

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